N-(1,1-dimethyl-2-morpholin-4-ylethyl)-2-{5-(4-fluorobenzyl)-3-[1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl]-1H-pyrazol-1-yl}acetamide → N-(1,1-dimethyl-2-morpholin-4-ylethyl)-2-[5-(4-fluorobenzyl)-3-(1H-1,2,3-triazol-4-yl)-1H-pyrazol-1-yl]acetamide

HRID 2074122Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2074122
[CH3:1][C:2]([NH:11][C:12](=[O:41])[CH2:13][N:14]1[C:18]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[CH:17][C:16]([C:27]2[N:28]=[N:29][N:30](CC3C=CC(OC)=CC=3)[CH:31]=2)=[N:15]1)([CH3:10])[CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1>C(O)(C(F)(F)F)=O>[CH3:10][C:2]([NH:11][C:12](=[O:41])[CH2:13][N:14]1[C:18]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[CH:17][C:16]([C:27]2[N:28]=[N:29][NH:30][CH:31]=2)=[N:15]1)([CH3:1])[CH2:3][N:4]1[CH2:5][CH2:6][O:7][CH2:8][CH2:9]1

Komponenten

3

Edukt 1

HCID 67091944N-(1,1-dimethyl-2-morpholin-4-ylethyl)-2-{5-(4-fluorobenzyl)-3-[1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl]-1H-pyrazol-1-yl}acetamide

Produkt 1

HCID 178448592N-(1,1-dimethyl-2-morpholin-4-ylethyl)-2-[5-(4-fluorobenzyl)-3-(1H-1,2,3-triazol-4-yl)-1H-pyrazol-1-yl]acetamideAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

A solution of N-(1,1-dimethyl-2-morpholin-4-ylethyl)-2-{5-(4-fluorobenzyl)-3-[1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl]-1H-pyrazol-1-yl}acetamide (1.3 g, 2.31 mmol) in TFA (30 mL) was refluxed overnight. The mixture was concentrated in vacuo and the residue was treated with water (30 mL) and CH2Cl2 (40 mL). The mixture was adjusted to pH 8-9 with Et3N. The organic layer was separated, dried over Na2SO4 and concentrated. The residue was purified via prep. HPLC to yield the title compound (380 mg, 38%) as yellow syrup. 1H NMR (400 MHz, MeOD) δ ppm 8.003 (s, 1H), 7.322 (m, 2 H), 7.100 (m 2 H), 6.399 (s, 1 H), 4.916 (m, 3 H), 4.089 (s, 2 H), 3.899-3.189 (m, 9 H), 1.472 (s, 6 H).

Aufarbeitung

  1. concentrationThe mixture was concentrated in vacuo
  2. additionthe residue was treated with water (30 mL) and CH2Cl2 (40 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified via prep

Quellen und Nachweise

ORD-Eintrag
ord-fea1a06f04d148d8a9122720b8f987ae
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07919488B2

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